Do I just schedule a trip and figure everything out later? Time off, etc?

Do I just schedule a trip and figure everything out later? Time off, etc? I really want to go to Porto, Portugal. I live in the United States, but my mom and grandparents and all my aunts and uncles were born in Portugal. They moved here when they were young, My mom was a teenager when she came over. Since then almost none of my family has been back, I visited the Azores this year and it was the most special trip I ha...

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